Head of Security Engineering & Risk - Director Level (Chicago) Job at Evolution USA, Chicago, IL

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  • Evolution USA
  • Chicago, IL

Job Description

This role is designed for a technically credible security leader who wants more than steady-state security operations.

Were partnering with a fast-scaling, private-equity-backed insurance agency operating across multiple business units and acquired entities. Security is already valued, the next step is to evolve it into a centralized, engineering-led security function capable of supporting continued growth.

Importantly, this role offers a natural progression into VP of Security and ultimately CISO, for someone who demonstrates both technical depth and executive judgement.

Your background:

Identity & Access Management (Foundational)

Identity underpins everything here.

You should bring strong hands-on experience with:

  • Microsoft Entra ID / Azure AD architecture and governance
  • Conditional Access, MFA strategy, Zero Trust identity models
  • Privileged Identity Management (PIM) and RBAC
  • Identity lifecycle management across employees, vendors, and acquisitions
  • SaaS security via SSO, SCIM, and risk-based access controls

This is a design-and-operate role, not just vendor oversight.

Endpoint, Device & User Security

Youll own protection for a highly distributed, business-critical user base.

Experience with:

  • EDR/XDR platforms (Defender, CrowdStrike, etc.)
  • Endpoint hardening across Windows/macOS
  • Device compliance and conditional access enforcement
  • Email security, phishing defense, and user-centric threat mitigation
  • Balancing real security with productivity and usability

Cloud & SaaS Security (Pragmatic, Not Theoretical)

This is a modern, SaaS-heavy environment.

You should be comfortable with:

  • Securing SaaS applications and cloud workloads
  • CASB / SaaS Security Posture Management concepts
  • Data protection, DLP, and sensitive data classification
  • Partnering with infrastructure and architecture teams on secure-by-design systems

Threat Detection, Monitoring & Incident Response

Youll be accountable for real outcomes, not just frameworks.

Hands-on exposure to:

  • SIEM and security monitoring platforms
  • Alert tuning and detection engineering
  • Incident response planning, tabletop exercises, and real incidents
  • Playbook creation and cross-functional coordination during security events

M&A & Multi-Entity Security (Highly Valued)

This company grows through acquisition, security must scale intelligently.

Relevant experience includes:

  • Supporting security due diligence during M&A
  • Integrating newly acquired companies into a common security baseline
  • Identity consolidation across tenants and environments
  • Managing risk pragmatically during post-acquisition transitions
  • Operating in environments where perfect isnt possible on day one

This is where experience and judgement matter more than theory.

MSP & Service-Provider Experience (Strong Plus)

Background in an MSP or services-led security environment is highly attractive.

Why?

  • Comfort operating across multiple clients, systems, and maturity levels
  • Strong troubleshooting instincts
  • Ability to prioritize risk quickly and communicate clearly
  • Experience owning outcomes without ideal conditions

Candidates with MSP experience often thrive in this role.

What Profile Fits Best

This role suits someone who has been:

  • A Senior Security Engineer, Security Architect, or Head/Director of Security
  • Operating in PE-backed, acquisitive, or multi-entity organizations
  • Comfortable being hands-on while shaping long-term strategy
  • Trusted to make risk-based decisions and explain them to executives

You dont need prior CISO title, but you should want that trajectory.

Career Progression

This is a deliberate succession role:

  • Short-term: Own and elevate the security engineering function
  • Mid-term: Step into VP-level ownership of security strategy and execution
  • Long-term: Grow into a CISO role, with board-level visibility and influence

The platform, sponsorship, and growth path are already in place.

Why High-Caliber Security Leaders Should Be Drawn to This Role

  • Real technical ownership, not checkbox security
  • Exposure to M&A, executive decision-making, and risk ownership
  • A leadership path thats earned , not promised
  • Enough complexity to stay interesting, without constant firefighting
  • Opportunity to build something durable and respected

Job Tags

Temporary work, Part time,

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